Dyestuff preparations for printing



Patented July 10, 1951 2,559,809 I C E DYESTUFF PREPARATIONS FOR PRINTING Arthur Topham, Blackley, Manchester, England,

assignor to Imperial Chemical Industries Limited, a corporation of Great Britain No Drawing. Application January 27, 1949, Se-

rial No. 73,237. In Great Britain January 26,

9 Claims.

This invention relates to dyestufi" preparations and more particularly it relates to dyestufi preparations containing leuco sulphuric ester derivatives of vat dyestufis for use in the printing of textile materials.

According to my invention I provide new dye stufi preparations for use in the printing of tex tile materials which comprise a leuco sulphuric ester derivative of a vat dyestuff and an organic compound containing a sulphonic acid group and a guanidine or substituted guanidine group.

The organic compounds used in my new dyestulT preparations have a solubilising or dispersing action on the leuco sulphuric esters.

As suitable organic compounds for use in the invention there may be mentioned phenylguanidine-p-sulphonic acid which may be obtained by condensing sulphanilic acid with cyanamide, guanidino-methane-sulphonic acid which may be obtained by condensing aminomethane-sulphonic acid with cyanamide and guanyltaurine which may be obtained by condensing taurine with cyanamide.

The leuco sulphuric ester derivative of a vat dyestufi used in the invention may be a derivative of a vat dyestufi of the anthraquinone, indigo or thioindigo series and it may be added to the dyestulf preparation in the form of a salt, for example the sodium salt.

If required urea may also be added to the dye-- stufi preparation.

The present invention is directed especially to the use of those leuco sulphuric ester derivatives which give sparingly soluble alkali metal or ammonium salts and which accordingly give weak and dull prints when used for printing textile fabrics by the conventional methods.

The new dyestufi preparations of my invention when made up into printing pastes by known methods give much brighter and stronger prints than those obtainable from the sparingly soluble leuco sulphuric ester derivative of the vat dyestuff in the absence of the organic compound as hereinbefore defined.

The invention is illustrated but not limited by the following examples in which the parts are by weight.

' Example 1 10 parts of a dyestufi paste containing of the sodium salt of the acid sulphuric ester of leuco-dibromanthanthrone,

10 parts of urea 5 parts of phenylguanidine-p-sulphonic acid are dissolved in 12 parts of water. The solution is added to parts of starch tragacanth thickening and 3 parts of a 30% sodium nitrite solution are then added.

100 parts The printing paste so obtained is printed onto cotton fabric. The fabric is dried and the prints developed by padding the fabric through 2% sulphuric acid solution at C., then rinsing and soaping at the boil. A very bright, level and strong orange print is obtained.

In the above example the phenylguanidine-psulphonic acid may be replaced with substantially the same result by guanidino-methane-sulphonlc 0 acid or by 2-guanidino-ethane-sulphonic acid or by N :N-dimethyl-N'-p-sulphopheny1 guanidine (which may be prepared by condensing dimethylcyanamide with sulphanilic acid) or by N:N"-dimethyl-N"-sulphophenylguanidine (which may be prepared by methylating N-phenyl-N-methyl 'thiourea with dimethyl sulphate basifying the aqueous solution of the product to precipitate NzS-dimethyl N -phenylisothiourea, sulphonating to give N :S-dimethyl-N-su1phophenylisothiorea and warming the latter with aqueous "methylamino solution), or by N-methyl-N-sulphophenylguanidine (which may be prepared'by sulphonation of N-methyl-N-phenylguanidine hydrochloride) or by N:N'-dimethyl-N-sulphophenylguanidine (which may be prepared by methylating Nphenyl-N-methyl-thiourea with dimethyl sulphate basifying the aqueous solution of the product to precipitate NzS-dimethyl-N- phenyl-isothiourea, converting this to the hydrochloride and sulphonating to give NzS-dimethyl- N-sulphophenylisothiourea and warming the latter with aqueous methylamine solution), or by N-methyl-N' -benzyl-N' sulphophenylguanidine which may be prepared by heating N S-dimethyl- N-sulphophenylisothiourea with aqueous benzyl amine solution) or by N:N:N-trimethyl-N'- sulphophenylguanidine (which may be prepared by warming N:S-dimethyl-N-sulphophenylisothiourea with aqueous dimethylamine solution).

Example 2 parts The paste so obtained is printed onto cotton fabric. The fabric is then dried and the print is developed by steaming during 10 minutes, rinsing in wateriiandzjsoaping at theboil." Ayers.

bright, level and strong orange print is obtained. In the above example the phenylguanidine-p;

sulphonic acid may be replaced with substantially the same result by NzN-dimethylNf pesulphoe phenylguanidine, or by -N:N-dimethyl-N.-sulr phophenylguanidine or by N :'NzN-trimethyl-'Nf-=-' sulphophenylguanidine.

I claim:

1. Dyestufi preparations for use-in the printing of textile materials comprising a-le'uco sul-phuric ester derivative of a vat dyestufi and a sulphonated guanidine of the formula /Ra "f*l-* Rl'ENRi. RI;

wherein-Blisa..radical selected from the group consisting of sulphonatedalkyl radicals and sulphonatedwmonocyclic aromatic hydrocarbon radicals .and'R RzRa -and R4 are selectedifrom the group :consisting .of ..hydrogen, a lower, alkyl and benzyl radicals;

2.-.:Dyestuff:-preparations.for-use in theprinting of textile: materials comprisinga leuco I sulphuric ester derivative of a vat dyestufi,and.-N:N:N trimethyleNi-sulphophenylguanidine..

3;. Dyestufi. preparations for .use: in' the. .print- '30 phuric ester.derivative of: a vat dyestufif and.

ing goi..textile.'materials comprisinga leuco. Sui-.-

N2N.-dimethyl-N-sulphophenylguanidine.

4.-..-Dyestuff preparations foruse-in the printing of a textile materials comprising a leuco sulphuric estenderivative of avat dyestuff and N-methyle N-sulphophenylguanidine- 5.: Dyestuffi preparations-for use in the rinting of textile materials-comprising aleuco-sulphuric 4 esteraderivative of" a vat;dyestufi, urea, and a sulphonated guanidihe of the formula R1 NR1 R4 whereinR isa radical selected from the group consistingQfsulphOnated alkyl radicals and sulphonated monocyclic aromatic hydrocarbon radicalsand. R1, R2; R2 and B4 are selected from the group consistingrofy hydrogen, lower alkyl and benzyl radicals.

6;i-Dyestuff preparations for use in the print ing of textile materials comprising a leuco sulphuric...ester derivativeofga vat .dyestufiand N: Ni-dimeth'yl-N -sulphophenylguanidine.-

'7..- Dyestuff. preparations. for use in the print.

ing of textile materials comprising a leuco. sulphuric ester derivative of a vat dyestuffandtN- methyl-N benzyl-N -sulphopheny1guanidine..

8. Dyestuff preparations as claimed in claim lwherein said leucosulphuric ester derivative .is;

in-theformof a sparinglysoluble alkali metal salt 9. Dyestuff preparations as claimed .in- :claim 1 wherein .saidleucosulphuric ester derivativezis in. the .-form-. of a sparingly soluble ammonium.

salt.

ARTHUR TOPHAML,

REFERENCES CITED The'following; references are of record in the file 'ofnthis :patent:

FOREIGN. "PATENTS N umber Country 1 Date 633,536 Great Britain Dec-.. 19,1949 235,027 Switzerland- .Malt. 1,.1945 

1. DYESTUFF PREPARATIONS FOR USE IN THE PRINTING OF TEXTILE MATERIALS COMPRISING A LEUCO SULPHURIC ESTER DERIVATIVE OF A VAT DYESTUFF AND SULPHONATED GUANIDINE OF THE FORMULA 